This Storied Tavern In Downtown San Antonio Celebrates 85 Years Of Revelry

After an extensive remodel, The Esquire Tavern returned to its original 1930s look.Kody Melton

The Esquire Tavern, one of San Antonio’s most beloved landmarks, is celebrating its 85th birthday on December 5, 2018. The oldest riverfront bar on the famous River Walk, The Esquire Tavern opened at 155 E. Commerce St. the day after Prohibition ended in 1933. The team will mark the occasion with an evening of revelry that will feature live music, a fortune teller, burlesque performances and a variety of complimentary hors d’oeuvres and drinks throughout the night.

At the time it opened, The Esquire was considered an opulent addition to Downtown San Antonio, with its high ceilings covered in pressed copper, terracotta floor tiles and elaborate woodwork. Thanks to its central location it drew a clientele from all walks of life, and later became an obligatory stop for visitors to the Alamo City looking to enjoy an inexpensive drink at the 100-foot bar, which holds the title of the longest in Texas.

The Esquire Tavern, shortly after opening in December 1933.Courtesy of Chris Hill

Since then, it has had just four owners. Rick Grinnan bought the property from George Georges in 1981 but kept it mostly intact. On the opposite side of the bar, original wooden booths flanked the long and narrow room, each with an individual jukebox playing a mix of early rock ’n roll classics and Tejano music legends. The bar served cold beer and simple drinks like Presidente Brandy and coke at prices that seemed stuck in the 1950s. Vicenta Lozano, known as “The Taco Lady” for more than 50 years, sold homemade taco plates for almost nothing. At the end of the bar, the room opened to hold a few tables and a tiny balcony, prime spot for watching tourist cruising the San Antonio river.

A view of the historic wooden bar, which at 100-ft. holds the title of Longest Bar in Texas.Kody Melton

The storied bar also enjoyed a bit of a reputation, with legends of gun fights, illegal gambling, and even a ghost roaming in the basement. There was a feeling of danger as you went through the doors, but more like reliving a movie scene in a seedy bar full of characters than fearing for your life. Old regulars perched at the bar smoking, a uniformed man frisking people at the door and the occasional over-served patron being escorted out just added to the charm. There was no better place in Downtown San Antonio to celebrate the Spurs’ championships, with beer flowing and strangers hugging each other in a packed house.

When plans to renovate the property with the addition of a hotel above the bar fell through, Grinnan decided it was best to sell The Esquire for financial reasons. In 2008, Christopher Hill stepped in as owner and shut down the bar for extensive renovations. When the doors opened again in January 2011, the changes were bittersweet. Gone was the underground element and the smell of smoke and Lone Star beer. The ceiling gleamed, the booths were reupholstered, and the little jukeboxes removed. The bar was reconfigured, adding much-needed new bathrooms. Even a detail as simple as the rococo wallpaper, installed in the 1960s, was painstakingly thought out to bring The Esquire back to its former elegance, re-creating the design but making it look like it had endured 50 years of smoke.

"In some ways, 85 years seems like a very long time, although my 96-year-old father might disagree,” says Hill. “The Esquire opened on a seminal day. It was probably visited more by the police in the seventies than by tourists to the Alamo, and once had a “VIP” room that rented for $20.”

A spicy Mexican beer cocktail, a michelada is the perfect libation to enjoy on a sunny day on the River Walk, with a tequila chaser.Kody Melton

Hill brought in Austin’s David Alan and San Antonio native Jeret Peña to revamp the beverage program. The new menu focused on pre-Prohibition cocktails, craft beers and an impressive selection of agave spirits, earning a James Beard award nomination. Hill also added a kitchen, offering elevated Texas cuisine and bar snacks to match the drinks and vibe, with Chef Brooke Smith at the helm. "As a San Antonio native, it has been an exciting journey to see Esquire Tavern's menu evolve,” says Smith. “I grew up dining all around San Antonio and now I am able to bring new flavors and dishes to a historic San Antonio landmark.”

The Esquire's bar program centers in classic cocktail staples like the French 75, once named after a small, powerful gun used during World War I and the Old-Fashioned, believed to stem from Prohibition when drinkers used muddled fruit to mask the flavors of bad booze. The Pimm's Cup, Pimm’s no. 1, cucumber, lemon, and house-made ginger beer, is a refreshing alternative.

Refreshing and classic, the Pimm's Cup is one of the showpieces in The Esquire's menu of traditional cocktails.Kody Melton

House specialties like the Commerce Street Fix - blanco tequila, chartreuse, pineapple, lemon and angostura bitters shaken and served on crushed ice - have earned the bar program, under the direction of current Beverage Director Houston Eaves, another Beard nomination.

The Commerce Street Fix is one of the most popular signature cocktails at The Esquire.Kody Melton

The lower level space, which opens to the River Walk and stood empty for a decade, opened 2 years ago as Downstairs at Esquire with a different concept and atmosphere. While upstairs channels a convivial saloon vibe, Downstairs is an intimate space with a unique décor inspired by Victorian botanical and zoological collections. Under Hank Cathey, the bar features boutique libations, an amazing selection of mezcales and a menu of bar snacks that includes a superb charcuterie and cheese board.

Downstairs at The Esquire is a more intimate space with a chill vibe and a superb selection of boutique spirits and mezcales.Kody Melton

"The Esquire Tavern continues to be the standard-bearer of bar excellence in San Antonio, and we aim to share our enthusiasm for great drinks and the people who make them with our guests,” says Eaves. “[The bar business] is a people business, and The Esquire would not have withstood the test of time without many people over the course of 85 years, including our exceptional team working hard day in and day out to share our little piece of San Antonio with the world. Here's to them, the many thousands of guests who have enjoyed the comforts of The Esquire Tavern over the decades, and those to come in the next 85 years."

“Times change,” says Hill. “We’ve been honored with two James Beard nominations since we spruced things up nearly eight years ago. We are honored to be thought of as an iconic part of San Antonio's 300-year history."

I'm a Mexico City-born writer based in Austin, Texas covering dining, drinking and travel since 1999. I think globally, widely interested in local ingredients and sustainability in the food chain, and love a restaurant with a good wine list and a sense of place. I have trave...